The Pleasure Chest is the oldest and most trusted sexuality boutique in the country, and we understand the importance of discretion. We ship every order in a plain brown box, with PC LTD on the return address. PC LTD (not The Pleasure Chest) will appear on your credit card statement.

Maybe you’ve never had one, maybe you have but you’re still not sure what all the fuss is about, or maybe you’re an orgasm overachiever with an unquenchable thirst for knowledge. Whatever your reason for taking this class, you’ll learn all about anatomy, techniques for coming with a partner or solo, how masturbation can help you expand your orgasm, G-spot orgasms, anal orgasms, and, of course, our Sex Specialists’ favorite tips and toys.

Want to have him squirming in his seat? Our Sex Specialists will show you how to use your mouth, hands, and more to give mind-blowing blow-jobs. We’ll cover male anatomy, tips and tricks, the truths and myths of “deep throat” plus other sexy secrets that are sure to have him begging for more.

Too often, the G-spot is described as a myth or a too-good-to-be-true orgasm button. Our Sex Specialists are here to set the record straight and teach you some real world techniques for enjoying your G-spot with or without a partner. We’ll cover massage, toys, the best positions for G-spot access, and even tricks for teaching yourself to squirt!

Want to have him squirming in his seat? Sex Nerd Sandra will show you how to use your mouth, hands, and more to give mind-blowing blowjobs. We’ll cover male anatomy, tips and tricks, the truths and myths of “deep throat” plus other sexy secrets that are sure to have him begging for more.

Get your laughs and lube in the same place. Join us for the return of the ever popular Performance Anxiety, a comedy night hosted by Eli Olsberg. For seven bucks, you can enjoy free beer, 15% off your purchases and live performances by some of the best comics working today.

Do you want to explore BDSM in the bedroom? Let Mistress Mary show you how to plan a kinky scene, from negotiation to aftercare. We’ll discuss safety and communication, how to choose quality implements, and the basics of bondage, roleplay and more. Open to beginners and seasoned players alike. Singles welcome!

It’s time for your weekly fix of Sex is Back: real people talking about their sex lives on camera.

This week, sex educator Lady Cheeky describes her sexual awakening at age 40, while watching True Blood. If you’d like to see more, you can also catch her at The Pleasure Chest Los Angeles tomorrow night at her body positive workshop, Big Beautiful Sex.

A Primer on Swinging with Cooper Beckett
Wednesday, May 7th @ 8-10pm – FREE!Cooper Beckett, from the podcast Life on the Swingset, takes you through the common peaks and valleys of beginning swinging, covering jealousy, safer sex practices, communication and more. Whether you’re brand new to swinging, been doing it for years, or just fascinated by the idea, there’s something here for everyone.

Twisted Knitters, co-sponsored with Sex Positive Chicago
Tuesday, May 13th @ 7-9pm – FREE!With a 2014 reboot of our popular knitting night, Sex Positive Chicago hops on board to co-host the sexiest night of knitting in Chicago! Come out and play with yarn and enjoy yummy snacks and great conversation with the folks from both The Pleasure Chest and Sex Positive Chicago.

Blow Jobs & Beyond with Ash
Wednesday, May 14th @ 8-10pm – FREE!Want to have him squirming in his seat? Our Sex Specialists will show you how to use your mouth, hands, and more to give mind-blowing blowjobs. We’ll cover male anatomy, tips and tricks, the truths and myths of “deep throat” plus other sexy secrets that are sure to have him begging for more.

Performance Anxiety – Comedy Night at The Pleasure Chest
Monday, May 19th @ 8-10pm – FREE!Get your laughs and lube in the same place. Join us for Performance Anxiety, a comedy night hosted by Goodrich Gevaart and Kristin Clifford and featuring live performances by some of the best comics working today. As a bonus, all audience members get 15% off their purchases on the night of the show.

How to Drive a Vulva with Allison Moon
Wednesday, May 21st @ 8-10pm – FREE!
Learn how to navigate the twists and turns of female sexuality in a class designed for people of all genders. In this playful, informative 2-hour workshop lead by sapphic savant Allison Moon, you will learn all the basics, including the bits and pieces that make up female sexual anatomy, simple ways to communicate in the heat of the moment, and positions to avoid fatigue and generate the power you need to rock their world – plus a few super secret, lesbian-ninja techniques. You’ll come away with new confidence to please a vulva and the person it belongs to, no matter what your hands-on experience.

Toys for Boys with Louie
Wednesday, May 28th @ 8-10pm – FREE!Think adult toys are for women only? Au contraire! From prostate massagers and penis pumps to vibrating rings and sensual strokers, there are tons of toys to perk up your penis! We’ll introduce you to the best toys for boys, how they can enhance solo and partner sex, and how to “borrow” products that are marketed to women for your own personal pleasure.

Become acquainted with the arousing possibilities of strap-on sex. Our Sex Specialists will show you that strap-on sex can be fun for everyone! Among the subjects covered will be how to choose the best harness and dildo for you, enhancing mutual satisfaction, owning your strap-on cock, and why and how strap-ons can be worn by guys too. A perfect class for beginners of any gender or orientation.

Can’t quite build the orgasms you want? Want to recapture that “one time?” Curious about multiple orgasms? Whatever your reason for taking this class, we will explore techniques for coming again and again with a partner and solo. The class will cover the ins and outs of the female pleasure system, simple techniques (including G-spot, Vaginal and Anal play) to expand your orgasms and get you on your way to multiple orgasms. Though this class is open to all genders and orientations, we will be focusing on orgasm for female-bodied people.

PlayboyTV’s Dr. Jess (Jessica O’Reilly) is coming to town to share her favorite moves from her bestselling book, Hot Sex Tips, Tricks and Licks. Laugh and learn as we cover seduction techniques, totally doable dirty talk and the hottest “finishing” moves with live demos (on carrots & peaches). A book signing and photo opportunity will follow. Open to all genders.

Learn how to make him moan and writhe in unbelievable pleasure. Join internationally-acclaimed sex educator Midori for this in-depth training on pleasuring your guy with hands, mouth and more! Using delicious practice props (think fruit!) you’ll learn all about the sucks, licks, swirls, strokes and touch secrets that will blow his mind. She’ll even cover tips on how to reduce discomforts or gag reflexes. What better gift is there than to show him your new techniques that very night?

Use the magic of Shaherezade! This class will teach you to incorporate seductive voice techniques to mesmerize your lover and transport both of you to an erotic landscape. Learn how to build and enrich a powerful fantasy, practice effective voice techniques and spellbinding. In this hands-on workshop, you’ll learn techniques for finding out both your fantasies, practice storytelling skills and learn to improve them with Midori’s gentle guidance. Couples and singles welcome.

Using restraint doesn’t have to be boring! Learn the essentials of light bondage, communication and negotiation, spanking, sensation play, and dirty talk. Our kink connoisseurs will teach you how to incorporate BDSM basics (and then some) into your sex life.

Looking for an all-over orgasm? Seeking the ever-elusive female ejaculation? This class will provide you with tips and techniques to expand your orgasm, both with your partner and on your own. For years the existence of the G-spot has been rejected while some have hailed it as the ultimate pleasure center; come find out what the buzz is about!

Annie will present an introductory slide show giving an overview of ecosex practices, art, fashion and green porn. Learn how to find your E-spot, and why switching the metaphor from “Earth as mother” to “Earth as lover” can create a paradigm shifting experience that can bring you more pleasure than ever. Try some ecosexual breathing, listen to ecosexy stories and explore pollen-amoury. It’s fun, a little kinky, and good for the Earth. By the end, you’ll likely discover that you are an ecosexual too!

Get your laughs and lube in the same place. Join us for the return of the ever popular Performance Anxiety, a comedy night hosted by Eli Olsberg. For seven bucks, you can enjoy free beer, 15% off your purchases and live performances by some of the best comics working today.

Get ready to celebrate Steak and a BJ Day in style! Porn star and sex educator extraordinaire Nina Hartley will show you how to use your mouth, hands, and more to give mind-blowing blowjobs. The class will cover male anatomy, tips and tricks, the truths and myths of “deep throat” plus other sexy secrets that are sure to have him begging for more.

Learn skills of communication and negotiation around BDSM with your partner and how it can be an intensely romantic journey between two (or more) people. Bondage, role play, sensation play – all of these things and more can be enjoyed within a loving relationship, whether monogamous or open. Our Sex Specialists will cover safety, tips, tricks, and how to choose quality implements. For beginners and seasoned players alike. Singles welcome too!

Looking for an all-over orgasm? Seeking the ever-elusive female ejaculation? This class will provide you with tips and techniques to expand your orgasm, both with your partner and on your own. For years the existence of the G-spot has been rejected while some have hailed it as the ultimate pleasure center; come find out what the buzz is about!

Get your laughs and lube in the same place. Join us for the return of the ever popular Performance Anxiety, a comedy night hosted by Eli Olsberg. For seven bucks, you can enjoy free beer, 15% off your purchases and live performances by some of the best comics working today.

In this workshop, no topic on taking it up the ass is taboo. Learn why a warm-up is important before anal exercise, why lube is your butt’s BFF, and how building comfort and trust with your partner can dispel common concerns such as pain or cleanliness. We’ll show you our favorite toys, how to use them solo or with a partner, cover the perks of having a prostate, anal G-Spot stimulation, and toy and partner safety.

Want to have him squirming in his seat? Our Sex Specialists will show you how to use your mouth, hands, and more to give mind-blowing blowjobs. We’ll cover male anatomy, tips and tricks, the truths and myths of “deep throat” plus other sexy secrets that are sure to have him begging for more.

This Boylesk intensive class focuses on the bare bones (yes, there’s more than one) of male striptease! Using a variety of dance, theater, and clowning exercises, you’ll get your feet wet and your fly unzipped in the world of Boylesk performance art!

Looking for an all-over orgasm? Seeking the ever-elusive female ejaculation? Sex educator extraordinaire (and manager of our Chicago store) Sarah Sloane will provide you with tips and techniques to expand your orgasm, both with your partner and on your own. For years the existence of the G-spot has been rejected while some have hailed it as the ultimate pleasure center; come find out what the buzz is about!

Is your bedroom buddy just begging for a pegging? In this workshop, we’ll teach you how to get your guy on-board for some ass loving. If you don’t know how to approach the subject (or their sphincter), we’ll give you tips on communication, the pleasures of perineum and prostate play, strap-on sex, anal sex safety, and the best toys and tricks to arouse him anally. This class will focus on bending over your boyfriend, but all genders and orientations are welcome.

You’re loaded with assets. Join sex icon Ducky DooLittle and explore ways to make the most of what you’ve got, from your hips, to your lips, to your finger tips. Learn all about a man’s pleasure anatomy, including his hottest spots and how to stimulate them. Discover tips and techniques that will have him melting in your mouth and in your hands. Explore sex secrets and desires guys are too shy to tell you, how to define what makes you sexy in his eyes and fresh communication techniques that will have him eagerly asking how he can please you in return.

Plus, give every weekend a lascivious twist with Sleazy Saturdays. Come mingle in our new store, talk sex with the staff, and stock up for Saturday night. From 4PM to 6PM, we’ll provide the booze and a variety of exciting entertainment.

What are open relationships and how do they work? From polyamory and consensual non-monogamy to swinging, we’ll explore how to negotiate these often challenging relationship models. Learn the pleasures and pitfalls of open relationships, improve communication and discover how to find other non-monogamous people.

Looking for an all-over orgasm? Seeking the ever-elusive female ejaculation? This class will provide you with tips and techniques to expand your orgasm, both with your partner and on your own. For years the existence of the G-spot has been rejected while some have hailed it as the ultimate pleasure center; come find out what the buzz is about!

If you haven’t thought about your prostate, you’re behind the times! Unofficially known as the male G-Spot, the prostate is actually central to the male orgasm & can provide amazing pleasure, either solo or with a partner. Our Sex Specialists will explain the role of the prostate, both physically & sexually, and offer tips and techniques to bring out the best in your bottom!

Want to give an even better blowjob? Let our Sex Specialist show you some new tricks and techniques. Learn how to find the perfect grip and mouth movement. Discover how to use your whole body to go the distance. Find new ways to tailor your blowjob to your specific partner. This class is for anyone who feels confident in giving head, but wants to take their skills to the next level.

With a 2014 reboot of our popular knitting night, Sex Positive Chicago hops on board to co-host the sexiest night of knitting in Chicago! Come out and play with yarn and enjoy yummy snacks and great conversation with the folks from both The Pleasure Chest and Sex Positive Chicago.

Wanna play doctor and patient? Or master and servant? Learn how to craft exciting and fun roleplay scenarios. We’ll cover the basics of safe, sane and consensual fantasy fulfillment, including negotiation, costumes, games, props and more.

Our Sex Specialists have the lady-loving tips and tricks to make you more pleasure proficient. Discover techniques for expanding a woman’s orgasm, out-of-this-world oral sex, G-spot stimulation, and much more! Whether solo or with a partner, this class is perfect for anyone interested in being a connoisseur of female sexuality.

Who says that Valentine’s Day has to be all about hearts and flowers? This class will teach you how to please your partner using dirty language, prurient pillow talk, and filthy fantasies, for a truly salacious celebration of love. We’ll help you find the scenarios that make you the hottest, move past giggle fits gracefully, and embody an extra-sexy alter ego.

Activist Melinda Chateauvert will be reading from her new book, Sex Workers Unite: A History of the Movement from Stonewall to Slutwalk, a provocative history that reveals how sex workers have been at the vanguard of social justice movements for the past fifty years while building a movement of their own that challenges our ideas about labor, sexuality, feminism, and freedom.

Learn how to take it off like a pro! Join Sex Specialist Kitty Cadillac as she shows you how to tantalize and tease your lover in the bedroom. Put on a private show they won’t forget. She will guide you through hot exotic dance moves, sensual glove and stocking peels, and how to give a sexy lap dance. It’s role playing at its finest!

Get your laughs and lube in the same place. Join us for the return of the ever popular Performance Anxiety, a comedy night hosted by Eli Olsberg. For seven bucks, you can enjoy free beer, 15% off your purchases and live performances by some of the best comics working today.